Isophthalic acid

16613

166.13

204-506-4

X35216H9FJ

0500

15310

DTXSID3021485

Crystalline powder|Colorless crystals|Needles from water or alcohol

29173980

74.6

1.7

White to off-white; Crystalline Powder

1.507 g/cm³ @ Temp: 20 °C

347 °C

100 °C

217.3±20.5 °C

1.5100 (estimate)

H2O: 001 g/100 mL (25 ºC)

Store below +30°C

2.6X10-8 mm Hg at 25 deg C(est)

Henry's Law constant = 2.18X10-12 atm-cu m/mol at 25 °C(est)

pKa1 = 3.70; pKa2 = 4.60 at 25 °C

Heat of formation: -802 kJ/mol at 25 °C|Heat of sublimation: 106.7 kJ/mol at 25 °C|log Kow = -2.34 at pH 7 (OECD 107 method)|Hydroxyl radical reaction rate constant = 1.3X10-12 cu cm/molecule-sec at 25 °C (est)

Dust forms explosive mixture in air (USCG, 1999).

Acids, Carboxylic

ISOPHTHALIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

700 °C

Dust explosion possible if in powder or granular form, mixed with air.

1.0921X10+8 J/kmol at the melting point of 619.15 K (346 °C)

Critical temperature = 1007.00 K; Critical pressure = 3.9500X10+6 Pa

NONH for all modes of transport

2

36/37/38

24/25-36-26

NT2007000

Xi

Stable. Incompatible with strong oxidizing agents, strong bases.

P264, P280, P305+P351+P338, P33, P313

H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Isophthalic acid is an indirect food additive for use only as a component of adhesives.

Behavior in Fire: Dust forms explosive mixture in air. (USCG, 1999)|Combustible. Finely dispersed particles form explosive mixtures in air.

Not Classified

Fire Extinguishing Agents: Water, dry powder, foam, carbon dioxide (USCG, 1999)|Use water spray, foam, powder, carbon dioxide.

If without adequate ventilation, use respirator with dust filter, goggles, and gloves (USCG, 1999)

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

An eye irritant.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.

May cause mechanical irritation to the eyes.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use local exhaust.

Protective gloves.

Wear safety spectacles.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Isophthalic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

The fine particle emission rate of isophthalic acid from a boiler burning No. 2 distillate fuel oil was 217.4-243.4 pg/kJ(1). The concentration of isophthalic acid in smoke particles collected from the open burning of plastic bags, roadside litter and landfill trash was 2.8, 35.4 and 4.8 ng/mg respectively(2).

URBAN/SUBURBAN: Isophthalic acid was detected, but not quantified, in the gas phase of urban air in Belgium(1). It was identified in airborne particulate matter (prominent GC peak) from a suburban area 60 km northeast of Tokyo, Japan in April 1985(2). The ambient annual average concentration of isophthalic acid in fine particle organic compounds at four sites on a west to east trajectory, West Los Angeles, downtown Los Angeles, Pasadena, and Rubidouc for 1982 were 2.1, 3.4, 2.9 and 2.1 ng/cu m, respectively(3); 24-hr samples were collected at 6 day intervals throughout the year; the concentration of isophthalic acid at a background site on San Nicolas Island, west of Los Angeles, averaged <0.03 ng/cu m from July to December(3). A study was performed of the long-term transport of photochemical air pollution from coastal areas in Japan with large emission sources to inland mountains(4); the resulting mean concentration of isophthalic acid in airborne aerosols in a plume at Takasaki (July 26-31, 1986) and Karuizawa (July 29-31, 1986) was 2.2 and 1.3 ng/cu m, respectively(4). The ratio of carboxylic acids to acetylene (which is believed to be derived from the same sources) increased during the day and decreased at night and averaged 72% at Takasaki and 84% at Karuizawa, suggesting that isophthalic acid is almost entirely formed photochemically during long-term transport(4). Airborne particulate matter (PM2.5 fraction) collected from eight sites in the southeastern US in 1999 and 2000 contained isophthalic acid concentrations ranging from 0.21 to 0.73 ng/cu m(5). Samples of atmospheric particulate matter collected at 12 sites in southern California in 1995 were found to contain average isophthalic acid concentration ranges of 0.233 to 0.616 ng/cu m(6). The concentration of isophthalic acid in the particulate matter of air samples collected at Fresno and Bakersfield CA (Dec 26, 1995 to Jan 6, 1996) ranged from 1.89 to 3.41 ng/cu m(7).|RURAL/REMOTE: The concentration of isophthalic acid in the particulate matter of air samples collected at the Kern Wildlife refuge in CA (Dec 26, 1995 to Jan 6, 1996) ranged from 0.349 to 0.433 ng/cu m(1).|SOURCE DOMINATED: The isophthalic acid concentration in the particulate-phase of air collected from a roadway tunnel in California was 157.5 ug/L(1). An isophthalic acid concentration range of 28.4 to 107 ng/cu m was detected in air samples (PM2.5 particulates) collected inside the Shing Mun tunnel in Hong Kong between Aug 13, 2003 to Feb 25, 2004(2).

Isophthalic acid was detected in the organic film collected from indoor and outdoor windows from a site in Toronto Canada in July 2000(1).

LD50 Rat ip 13000 mg/kg bw|LD50 Rat oral 12200 mg/kg bw|LD50 Rat oral 13000 mg/kg bw|LD50 Rabbit dermal >2000 mg/kg bw|For more Non-Human Toxicity Values (Complete) data for ISOPHTHALIC ACID (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ No signs of toxicity were observed in Leuciscus idus melanotus (Golden orfe) exposed to IPA at levels of up to 895 mg/L (measured) for 96 hours under static conditions.|/AQUATIC SPECIES/ No signs of toxicity in terms of mortality or immobilization were observed in Daphnia magna (water flea) exposed to IPA at levels of up to 876 mg/L (measured) for 48 hours under static conditions.|/AQUATIC SPECIES/ No adverse effects on growth were observed in Scenedesmus subspicatus (green algae) exposed to IPA at levels of up to 969 mg/L (measured) for 96 hours under static conditions.|/AQUATIC SPECIES/ In activated sewage sludge, toxicity to bacteria, as indicated by inhibition of oxygen consumption, was evident with a EC50 value of 617 mg/L.

Isophthalic acid was an oxidation product of Singletary Lake (a freshwater lake in eastern North Carolina) fulvic acid(1).

Isophthalic acid's production and use as a raw material in the production of unsaturated polyester resins, alkyd coatings, other polymers and derivative chemicals(1) may result in its release to the environment through various waste streams(SRC). There are industrially important esters of isophthalic acid such as dimethyl isophthalate that may undergo chemical or enzymatic hydrolysis to yield isophthalic acid(2,3).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 79(SRC), derived from a molecular structure estimation method(2), suggests that isophthalic acid will have high mobility in soil(SRC). It is a dibasic (2 displaceable hydrogen atoms) acid whose pKa1 is 3.70 and pKa2 is 4.60 at 25 °C(3) and will primarily exist in the anion form in the environment and form salts with cations in soil; anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of isophthalic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(5). It absorbs UV radiation >290 nm(6), and therefore may degrade by direct photolysis on the soil surface(SRC). Isophthalic acid is readily biodegradable in screening tests using sewage sludge(7-10) and may be expected to biodegrade in soil(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 79(SRC), determined from a structure estimation method(2), indicates that isophthalic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Isophthalic acid is a dibasic (2 displaceable hydrogen atoms) acid whose pKa1 is 3.70 and pKa2 is 4.60 at 25 °C(5) and will be largely dissociated in at an environmental pH range of pH 5 to pH 9(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 1.66(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. Isophthalic acid absorbs UV radiation >290 nm(9), and therefore may be susceptible to direct photolysis in surface waters(SRC). Isophthalic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Isophthalic acid has been shown to be readily biodegradable in screening studies(10-13) and is expected to biodegrade in natural water(11).|ATMOSPHERIC FATE: According to a theory of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isophthalic acid, which has an estimated vapor pressure of 2.6X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Its existence in the atmosphere in both phases has been observed experimentally(3,4). Vapor-phase isophthalic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(5). Particulate-phase isophthalic acid may be physically removed from the air by wet and dry deposition(SRC). Isophthalic acid absorbs at wavelengths >290 nm(6), and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of isophthalic acid with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Isophthalic acid absorbs UV radiation >290 nm up until about 330 nm(2), and therefore it may be susceptible to direct photolysis by sunlight(SRC). Isophthalic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Isophthalic acid is a dibasic (2 displaceable hydrogen atoms) acid whose pKa1 is 3.70 and pKa2 is 4.60 at 25 °C(4); therefore isophthalic acid will be largely dissociated in the environment and form salts with cations(SRC).

An estimated BCF of 3 was calculated in fish for isophthalic acid(SRC), using a log Kow of 1.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of isophthalic acid can be estimated to be 79(SRC). According to a classification scheme(2), this estimated Koc value suggests that isophthalic acid is expected to have high mobility in soil(SRC). Isophthalic acid is a dibasic (2 displaceable hydrogen atoms) acid whose pKa1 is 3.70 and pKa2 is 4.60 at 25 °C(3) indicating that isophthalic acid will be largely dissociated in the environment in the anion form and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for isophthalic acid is estimated as 2.2X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that isophthalic acid is expected to be essentially nonvolatile from water surfaces(2). Isophthalic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Isophthalic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0675 mm Hg at 100 °C(3).

DRINKING WATER: Isophthalic acid was identified as a by-product of ozone disinfection of drinking water(1).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of isophthalic acid is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 117,411 workers (17,858 of these were female) were potentially exposed to isophthalic acid in the US(1). Monitoring data indicate that the general population may be exposed to isophthalic acid via inhalation of ambient air and ingestion of drinking water(SRC). Some potential for occupational exposure to isophthalic acid via the inhalation and dermal routes is possible during bag filling operations and while loading rail cars and trucks; typical exposures for unit operators, baggers/loaders and forklift operators working in isophthalic acid manufacturing range from <0.04 to 2.92 mg/cu m(2).

Blood levels of /Isophthalic acid/ (IPA) were detected immediately following exposure to rats at 10 mg/cu m for 6 hr/day. These levels remained elevated throughout the exposure period. Serum IPA concentrations detected in female rats (5.3-9.3 ug/mL) were consistently higher than the concentrations detected in male rats (1.4-3.4 ug/mL). The data suggest that steady state is achieved fairly rapidly (on the first day of exposure). One week following exposure, IPA was not detected in blood, indicating that clearance of IPA from the body occurs fairly rapidly. Based on a log Kow value of -2.34, IPA is not expected to accumulate appreciably in tissues, and is likely to be readily excreted from the body.|Blood levels of /Isophthalic acid/ (IPA ) ... (determined as total mg phthalate/L) collected during a 13-week feeding study (in rats) were increased in a dose-dependent manner on days 7, 30, 60, and 90. ... Results from 24-hour urines collected on days 7, 30, 60, and 90 indicate that urinary excretion, presumably as unchanged chemical, is the primary route of elimination for ... IPA. ...

Some activity was noted by renal enzymes in the formation of monoester from the correspondlng diesters; only very weak activity for the cleavage of the monoesters was seen. Compared with the formation rate of terephthalic-acid from di-n-butyl-terephthalate, the rate of isophthalic-acid formation from di-n-butyl-isophthalate was more than twice as high with renal enzymes. Half ester formation rate was relatively rapid in all preparations. Acid formation was slow. This suggested that acid formation was the rate limiting step.

Impurities in isophthalic acid, other than isomeric ones, include reaction intermediates, eg, 3-formalbenzoic acid and m-toluic acid; by-products, eg, benzoic acid; and residual metals

May cause slight to moderate irritation of eyes, skin, and mucous membranes on prolonged contact. Ingestion may cause gastrointestinal irritation. (USCG, 1999)

INHALATION: remove victim to uncontaminated area; get medical attention if complications arise. INGESTION: get medical attention if complications arise. EYES: flush with large amounts of water for 15 min.; get prompt medical attention. SKIN: wash with water. (USCG, 1999)

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

isophthalate

The substance can be absorbed into the body by ingestion.

Redness.

ABOUT 54% AS A CHEM INT FOR ISOPHTHALIC POLYESTER RESINS; ABOUT 26% AS A CHEM INT FOR ALKYD RESINS; ABOUT 1% AS A CHEM INT FOR THE PLASTICIZER DIOCTYL ISOPHTHALATE; AND ABOUT 19% IN OTHER APPLICATIONS (1974)|MORE THAN 50% ... USED TO PREPARE ISOPOLYESTERS, SECOND LARGEST USE ... IS IN ALKYD RESINS (1982)|More than 50% is used to prepare unsaturated polyester resins. Second largest use is in alkyd resins.

Grade: Technical.|Three grades available (from Amoco) IPA-85: 82% (by wgt) isophthalic acid, IPA-99 and IPA-220: 98.5% (by wgt) isophthalic acid

Adhesive manufacturing|1,3-Benzenedicarboxylic acid: ACTIVE|Isophthalic acid is presently manufactured commercially by the oxidization of m-xylene.|The chemistry of the oxidation is similar to that of p-xylene and liquid-phase production facilities often can be used interchangeably for isophthalic acid and terphthalic acid.|The quality of isophthalic acid produced by air oxidation of m-xylene is suitable for most applications. For special applications it is purified .... dissolved in water, treated catalytically, recrystallized, separated, and dried.|Further purification was generally not carried out in the past, but a purified grade that is now being produced will become the standard.

A comparative high-pressure liquid chromatography (HPLC) analysis of monomers, terephthalic acid (TPA), isophthalic acid (IPA), and dimethyl terephthalate (DMT) from polyethylene terephthalate (PET) food containers was conducted. Monomer linearities and sensitivities were calibrated between established and novel HPLC analyses. Safety of PET containers was evaluated with newly established detection methods for TPA, IPA, and DMT. Migration of the 3 monomers into food simulants (water, 4% acetic acid, 20% alcohol, and n-heptane) from 56 PET containers collected from open markets was monitored. Migrated monomers were not detected over 0.1 ppm of detection limit. The corresponding estimated daily intake was measured to confirm the safety of these publicly available PET containers and to permit comparison to the specific migration limit of the European Union. The estimated daily intake of 3 monomers migrating from PET was 0.0384 mg/kg each. This represented only 0.6% of the European Union's specific migration limit, confirming the safety of the examined containers.